Hydrochloric Acid → HCID 86750225, compound

HRID 234716Notes

Reaction equation

HRID 234716 reaction equation
[C:1]1([N:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:8](=[O:28])[NH:9][N:10]=[CH:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.O.C(O)(=O)C>[C:29]1([N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:28])[NH:9][NH:10][CH2:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 57100418HCID 57100418, compound

Product 1

HCID 86750225HCID 86750225, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the compound prepared in example 13 (291 mg) in methanol (6.5 ml) was added sodium cyanoborohydride (42 mg) and added dropwise followed by acetic acid (1.45 ml). The mixture was stirred overnight at room temperature. After acidified by adding 2N hydrochloric acid until pH 1, the mixture was stirred for 30 min. The mixture was diluted with water. After neutralized by adding sodium bicarbonate until pH 7~8, the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (235 mg) having the following physical data.

Workup

  1. additionadded dropwise
  2. stirringthe mixture was stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-9a9f28f54e7244c983b40014e58d9d85
Source dataset
uspto-grants-1997_01
Patent number
US05596009

Reaction notes

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